4-trifluoromethyl-2-nitrophenyl azide | 51093-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-trifluoromethyl-2-nitrophenyl azide
• 英文别名: 2-nitro-4-trifluoromethyl-phenylazide；1-azido-2-nitro-4-(trifluoromethyl)benzene
• CAS: 51093-74-4
• 化学式: C₇H₃F₃N₄O₂
• mdl: MFCD00211377
• 分子量: 232.122
• InChiKey: CCMJPJQJSXHJSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-trifluoromethyl-2-nitrophenyl azide 以 甲苯 为溶剂， 反应 2.0h， 生成 5-trifluoromethylbenzofuroxan
  参考文献：
  名称：

  Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

  摘要：

  Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy. Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy. The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells. Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and/or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells. Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced. Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxides have reduction potentials significantly more positive than Tirapazamine (E(pc)-0.90 V). The most potent cytotoxins to cells in culture were the 6,7,-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine. The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity. Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro. In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine. This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

  DOI：

  10.1021/jm00010a023
• 作为产物：
  描述：

  4-氟-3-硝基三氟甲苯 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 4-trifluoromethyl-2-nitrophenyl azide
  参考文献：
  名称：

  Click Variations on the Synthesis of 2-Nitrophenyl-4-aryl-1,2,3-triazoles without Isolation of 2-Nitrophenyl Azides

  摘要：

  我们报告了一系列高效的程序，用于制备2-硝基苯基-4-芳基-1,2,3-三唑，避免了分离潜在危险的2-硝基苯基叠氮化物。一种有机催化的叠氮-烯醇变体允许有效地获得目标化合物，同时还表明，从电子不足的芳基碘化物出发，涉及初步Sonogashira偶联的金属催化叠氮-炔烃程序是可行的。

  DOI：

  10.1055/s-0039-1691524
• 作为试剂：
  描述：

  4-氨基-3-硝基三氟甲苯 、 硫酸 、 sodium nitrite 、 尿素 、 叠氮化钠 、 、 在 ice 、 crude product 、 4-trifluoromethyl-2-nitrophenyl azide 、 氯仿 、 Sodium sulfate-III 作用下， 以 甲苯 、 水 、 溶剂黄146 为溶剂， 反应 18.33h， 生成 5-trifluoromethylbenzofuroxan
  参考文献：
  名称：

  Novel process for the synthesis of quinoxaline and benzimidazole-N-oxides

  摘要：

  使用一种新型工艺，通过苯并呋喃氧化物和含有活性亚甲基的化合物在碱性条件下的反应，合成了喹喹啉和苯并咪唑-N-氧化物以及3-羟基-2-喹啉羧酸的酯和酰胺衍生物。

  公开号：

  US04866175A1

文献信息

• The reactivity of organophosphorus compounds. Part XXX. Iminophospholes and a new synthesis of benzofurazans via intramolecular rearrangement of 1-o-nitroarylimino-1,2,5-triphenylphospholes
  作者：J. I. G. Cadogan、Robert J. Scott、Robert D. Gee、Ian Gosney

  DOI：10.1039/p19740001694

  日期：——

  1-aroylimino-1,2,5-triphenylphospholes (2; X = PhCO and p-NO2·C6H4CO), but these decomposed at this temperature to give the corresponding aryl cyanides and the phosphole oxide. The use of copper-bronze reduced the decomposition point of the dioxazolidin-2-ones sufficiently for the iminophospholes to be isolated. Base catalysed decomposition of ethyl N-(p-nitrophenylsulphonyloxy)carbamate (4) in the presence of

  已经合成了一系列的N-取代的1-亚氨基-1,2,5-三苯基磷（2）。芳基，甲磺酰基，芳基磺酰基，乙氧基羰基，苯氧基羰基和二苯基次膦酰基叠氮化物与1,2,5-三苯基膦的反应得到相应的N-取代的1-亚氨基膦[2; X = Ar，MeSO 2，ArSO 2，EtO 2 C，PhO 2 C和Ph 2 P（O）]，通过非亚硝基苯路线的收率很高。甲苯磺酰磷（2； X =甲苯磺酰基）也是通过无水氯胺-T反应制得的。与磷脂。苯甲酰叠氮化物通过分解反应，然后进行库尔修斯重排反应，而不是与相对较弱的亲核性1,2,5-三苯基磷脂反应（参见Ph 3 P）。缺电子的4-硝基苯甲酰基和2,4-二硝基苯甲酰基叠氮化物给出相应的1-芳基氨基-1,2,5-三苯基磷[2; X = C 6 H ^ 4 NO 2 - p和2,4-（NO 2）2 C ^ 6 ħ 3在6和55％的产率分别]。在铜存在下的5，7-二甲基四唑并[1，5-
• SNAr azidation of phenolic functions utilizing diphenyl phosphorazidate
  作者：Kotaro Ishihara、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tetlet.2019.151493

  日期：2020.2

  A useful method for the synthesis of aryl azides via SNAr reaction of phenol derivatives using diphenyl phosphorazidate (DPPA) as an azidation reagent was developed. Various phenol derivatives bearing electron-withdrawing groups were converted into the corresponding aryl azides in a single step. This method is easy to perform and enables the preparation of aryl azides without the use of explosive azide

  开发了一种有用的方法，该方法通过使用叠氮磷酸二苯酯（DPPA）作为叠氮化试剂通过苯酚衍生物的SNAr反应进行芳基叠氮化物的合成。带有吸电子基团的各种酚衍生物可在一个步骤中转化为相应的芳基叠氮化物。该方法易于实施，并且能够在不使用爆炸性叠氮化物源的情况下制备芳基叠氮化物。
• New 1,2,3-triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors. II
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Valerio Scartoni、Laura Betti、Gino Giannaccini、Maria Letizia Trincavelli

  DOI：10.1016/s0223-5234(02)01376-4

  日期：2002.7

  On pursuing research about 1,2,3-triazolo[1,5-a]quinoxalines, in this paper we report synthesis and binding assays toward the benzodiazepine and A(1) and A(2A) adenosine receptors, of a new series of derivatives, bearing some structural changes (introduction of fluorine and trifluoromethyl in the seventh position, amino substituents in the fourth position, benzyl group in the fifth position and aroyl

  在进行有关1,2,3-三唑并[1,5-a]喹喔啉的研究后，本文报道了一系列苯并二氮杂and以及A（1）和A（2A）腺苷受体的合成和结合测定衍生物，具有一些结构变化（在第七位引入氟和三氟甲基，在第四位引入氨基取代基，在第五位引入苄基，在第三位引入芳酰基取代基）。生物学测试表明，只有7-氟取代的化合物3a和4a以及N-苄基衍生物7对苯二氮杂pine受体具有良好的亲和力，而只有7-三氟甲基取代的化合物3b具有中等的亲和力且对A的选择性低。 （1）腺苷受体。其他结构修饰强烈降低了生物活性。
• Potential antileukemic and immunosuppressive drugs. 3. Effects of homocyclic ring substitution on the in vitro drug activity of 4-nitrobenzo-2,1,3-oxadiazoles (4-nitrobenzofurazans) and their N-oxides (4-nitrobenzofuroxans)
  作者：P. B. Ghosh、B. Ternai、M. W. Whitehouse

  DOI：10.1021/jm00273a012

  日期：1972.3
• 5-(4′-Substituted-2′-nitroanilino)-1,2,3-triazoles as new potential potassium channel activators. I
  作者：Giuliana Biagi、Vincenzo Calderone、Irene Giorgi、Oreste Livi、Valerio Scartoni、Barbara Baragatti、Enrica Martinotti

  DOI：10.1016/s0223-5234(00)00180-x

  日期：2000.8

  By the hypothesised correlation with the large conductance Ca++-activated potassium channel (BKCa) openers NS 004 and NS 1619, bearing a benzimidazolone ring, a series of new 5-(4'-substituted-2'-nitroanilino)-1,2,3-triazoles were synthesised and tested on in vitro isolated vascular preparation. The compounds were prepared. starting from the appropriately substituted 2-nitro-phenylazides by 1,3-dipolar cycloaddition reaction to cyanoacetamide and following Dimroth isomerisation of the corresponding 1-arylsubstituted-5-amino-1,2,3-triazoles. The analogous 5-(4'-substituted-2'-amino-anilino)-1,2,3-triazoles were also prepared to assess the role of the nitro group in the pharmacophoric model. Almost all the nitro compounds showed a vasorelaxant activity on endothelium-denuded rat aortic rings with a potency comparable to that recorded for the reference compound NS 1619. Such a vasorelaxing activity was significantly reduced by the increase of the level of membrane depolarisation and by the potassium channel blocker 4-aminopyridine with a pharmacodynamic behaviour consistent with a potassium channel activation. (C) 2000 Editions scientifiques et medicales Elsevier SAS.